Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 1,2,4-Triazine-3,5(2H,4H)-dione,2-(2,3,5-tri-O-acetyl-b-D-ribofuranosyl)-
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2169-64-4

2169-64-4 structure

Name: 6-AZAURIDINE 2',3',5'-TRIACETATE
Chemical Name: 6-azauridine 2',3',5'-triacetate
CAS Number: 2169-64-4
Molecular Formula: C₁₄H₁₇N₃O₉
Molecular Weight: 371.29900
Catalog: Signaling Pathways Anti-infection Influenza Virus
Create Date: 2018-12-30 01:37:07
Modify Date: 2026-08-02 17:58:03
Azaribine (2',3',5'-Tri-O-acetyl-6-azauridine) is a potent orotidine monophosphate decarboxylase (OMPD) inhibitor. Azaribine is an antiviral inhibitor of several RNA viruses and inhibits viral genome replication and gene transcription. Azaribine shows broad-spectrum antiviral activity (EC50=3.80 nM-1.73 μM against influenza A and B viruses; EC50=1.62 μM against ZIKV Paraiba). Azaribine, a triacetate salt of Azauridine, has the potential for psoriasis research[1][2].

Name	6-azauridine 2',3',5'-triacetate
Synonyms	EINECS 218-515-6 AZIBINE 4h)-dione,2-(2’,3’,5’-triacetyl-beta-d-ribofuranosyl)-as-triazine-5-(2h 2',3',5'-TRI-O-ACETYL-6-AZAURIDINE AZARIBINE 6-Azauridine 2',3',5'-triacetate 2’,3’,5’-Tri-O-acetyl-6-azauridine, Azibine, antineoplastic agent acetic acid [3,4-diacetyloxy-5-(3,5-dioxo-1,2,4-triazin-2-yl)-2-oxolanyl]methyl ester 6-Azauridine Triacetate cb304 2-BETA-D-RIBOFURANOSYL-1,2,4-TRIAZINE-3,5(2H,4H)-DIONE 2',3',5'-TRIACETATE nsc-67239 2-(2’,3’,5’-triacetyl-beta-d-ribofuranosyl)-as-triazine-3,5-(2h,4h)-dione 2’,3’,5’-triacetyl-6-azauridine (-)-6-AZAURIDINE 2',3',5'-TRIACETATE 2',3',5'-triacetyl-6-azauridine 2μ,3μ,5μ-Tri-O-acetyl-6-azauridine, 6-Azauridine 2μ,3μ,5μ-triacetate, 6-AzUrd-TA, Azibine, 2-β-D-Ribofuranosyl-1,2,4-triazine-3,5(2H,4H)-dione 2μ,3μ,5μ-triacetate 2-(2-O,3-O,5-O-Triacetyl-β-D-ribofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione 1,2,4-Triazine-3,5(2H,4H)-dione, 2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl) 2-BETA-D-RIBOFURANOSYL-AS-TRIAZINE-3,5(2H,4H)-DIONE 2',3',5'-TRIACETATE (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(3,5-dioxo-4,5-dihydro-1,2,4-triazin-2(3H)-yl)tetrahydrofuran-3,4-diyl diacetate 6-Azauridine 2μ,3μ,5μ-triacetate, 6-AzUrd-TA, Azibine 6-AZURD-TA 6-azauridine-2',3',5'-tri-O-acetate triacetyl-6-azauridine ta-azur 2',3',5'-Tri-O-acetyl-6-azauridine\|\|\|NSC

Description	Azaribine (2',3',5'-Tri-O-acetyl-6-azauridine) is a potent orotidine monophosphate decarboxylase (OMPD) inhibitor. Azaribine is an antiviral inhibitor of several RNA viruses and inhibits viral genome replication and gene transcription. Azaribine shows broad-spectrum antiviral activity (EC50=3.80 nM-1.73 μM against influenza A and B viruses; EC50=1.62 μM against ZIKV Paraiba). Azaribine, a triacetate salt of Azauridine, has the potential for psoriasis research[1][2].
Related Catalog	Signaling Pathways >> Anti-infection >> Influenza Virus Research Areas >> Infection Research Areas >> Inflammation/Immunology
In Vitro	Azaribine (2',3',5'-Tri-O-acetyl-6-azauridine; 0-2 μM; 48 小时) 对MDCK细胞具有细胞毒性 (MTT: CC50=19.66 μM)[1]。 Azaribine 对 BIRFLU 增殖具有强效抑制作用 (MDCK 细胞: EC50=0.29 μM；A549 细胞: EC50=0.55 μM) [1]。 Azaribine 在 MDCK 细胞后处理期间显示出对季节性 H1N1 和 H3N2 IAV 和 IBV 的抑制作用，EC50 分别为 0.60 μM、0.77 μM、0.80 μM[1]。 Azaribine 在 16HBE 细胞的后处理过程中具有抗 NC H1N1 作用，EC50 为 1.58 μM[1]。 Cell Cytotoxicity Assay[1] Cell Line: MDCK cells Concentration: 0-2 μM Incubation Time: 48 h Result: Had cytotoxicity on MDCK cells (CC50=19.66 μM).
References	[1]. Jun-Gyu Park, et al. Identification and Characterization of Novel Compounds with Broad-Spectrum Antiviral Activity against Influenza A and B Viruses. J Virol. 2020 Mar 17;94(7):e02149-19. [2]. Desarey Morales Vasquez, et al. Identification of Inhibitors of ZIKV Replication. Viruses. 2020 Sep 18;12(9):1041.

Density	1.6g/cm3
Melting Point	99-101ºC(lit.)
Molecular Formula	C₁₄H₁₇N₃O₉
Molecular Weight	371.29900
Exact Mass	371.09600
PSA	155.88000
Index of Refraction	1.621

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XY8577000

CHEMICAL NAME :: as-Triazine-3,5-(2H,4H)-dione, 2-(2',3',5'-triacetyl-beta-D-ribofuranosyl)-

CAS REGISTRY NUMBER :: 2169-64-4

LAST UPDATED :: 199612

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C14-H17-N3-O9

MOLECULAR WEIGHT :: 371.34

WISWESSER LINE NOTATION :: T6NNVMVJ B- CT5OTJ BOV1 DOV1 E1OV1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 5670 mg/kg/6W

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Blood - changes in cell count (unspecified)

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 108,272,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 12 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7800 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 321 gm/kg/15W-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Blood - changes in erythrocyte (RBC) count Related to Chronic Data - death

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - pig

DOSE/DURATION :: 30 gm/kg/14W-I

TOXIC EFFECTS :: Blood - changes in erythrocyte (RBC) count

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 17,511,1970

Safety Phrases	S22-S24/25
WGK Germany	2
RTECS	XY8577000

Precursor 2
54-25-1 108-24-7
DownStream 1
54-25-1

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